James Gallagher

great career paths are not linear

Published on April 9, 2020

I have trouble talking about my career path.

When I am asked the question “How did you get to where you are today?”, I am first confused by the point at which the other person expects me to begin talking about my journey. Then I get confused about what is relevant to my career and what is not.

It is stressful for me to talk about the path I have been on for these reasons.

Reflecting on my career path over the last few weeks has led me to an interesting realization: many of the best career paths are difficult to describe, and that is what made them such strong career paths.

Let me elaborate by using my career path as an example. I officially started my career at the age of sixteen, working as a writer and a researcher for a technology company. However, my career started before then. Before I applied for jobs I was writing every day, working on side projects, and explored a wide range of different fields.

Prior to joining a company, I had dipped my toe into venture capital, startups, programming, and a number of other fields, because I was not exactly sure what I wanted to do yet. Then, when I discovered writing, I realized it was an activity to which I wanted to commit more of my time. Initially, I did not see writing as a career -- it was a fun activity that took up a lot of my spare time -- but I quickly realized that there were in fact jobs available in writing.

What got me into my current position, though, was the career moat I had built up. For months before I started looking for a job, I had conducted research into Income Share Agreements, an alternative model of education financing.

Because very few people knew a lot about ISAs -- but so many people were talking about them -- there was a unique opportunity for me to pursue the field. If I took a chance on an emerging idea, then as more people pursued the field, I would be in a better position to build career capital and connections with other people.

This description misses out a wide range of paths I pursued. I did not mention how, at one point, I was thinking about founding my own company. I also did not discuss the times when I seriously entertained going to university. Those were all part of my path, too, but I don’t often talk about them because they don’t seem as relevant.

Great career paths are not always linear because what makes them great is that they are inconsistent. If there was a handbook on “how to become a researcher at 16,” my career path would not be seen as exceptional. It would be seen as normal. But that handbook did not exist, and so I used my time to write it myself.

When you ask a successful person what got them to where they are today, they often mention a high degree of luck. This luck, though, was actually a product of their labor. Most successful people explore a wide range of different ideas -- and fail constantly -- before they find one that sticks, and it is that idea with which their success is associated. They were able to become successful because they were not afraid to pursue a less-defined path.

There is a career arbitrage opportunity to be found in pursuing emerging ideas that you find unique and interesting without worrying about whether or not that idea will help you on your career path.

Many people make the mistake of thinking about careers as a linear path. “You must do X before you can do Y” is a common heuristic used to describe linearity in careers. Or, to use an example “You must go to college before you can start a startup”.

Thinking about careers as a linear path makes sense because it helps introduce some consistency into the puzzle. Something as important as your career path seems like something that should be consistent, and follow a clear, step-by-step line of progress. But that is not always the case, and if you can set aside that notion, you can do great things.

If you spend your time hacking around with new ideas, you are more likely to find a good one than someone who is operating within the confines of “you must do X before you can do Y.” Your path may be more uncertain, but that’s what makes it great. The uncertainty associated with non-linear career paths is what puts people off pursuing them, so if you are willing to embrace the uncertainty, there are many opportunities for growth.